The $600 Million Social Life Of Foursquare Founder Dennis Crowley

tantek via FlickrFor Dennis Crowley, life has always been a game that should be played with friends. Few people could turn that mentality into a $600 million business.

Dennis Crowley sold his first startup to Google. His second, Foursquare, has nearly 100 employees, 16 million users, and it is creeping towards a billion-dollar valuation.

Crowley is the poster child for New York's burgeoning tech scene, but his success didn't happen overnight.

It was a series of failures and disappointments.

Crowley chronicled the experience on a personal blog, Teendrama. We've read through that archive and spoken to Crowley, his family and his friends to learn how the party-prone teenager became one of the youngest, most successful entrepreneurs in the world.

Crowley grew up in a close-knit family that made everything playful. When they were in church, they'd create competitions to see how many hands each could shake during Peace Be With You.

"We'd flash the number to each other and be like 'Oh I got 6!' The family record is 15 or something," says Crowley.

Crowley and his ropommates pose with $1,600 and a police ticket.Teendrama
It wasn't long before these kinds of social games turned into a social business.

As an upperclassman at Syracuse University, Crowley and his friends threw parties for freshmen. Freshmen were unable to get into bars and they were desperate for alcohol. Crowley charged a cover at the door. One party alone made him $1,600.

"We made so much cash and eventually got busted by the cops," Crowley, then a Junior at Syracuse, wrote. "I ended up having to go to court with Kevin - we were charged with a simple noise disturbance violation and paid nothing. Aw-yeah."